<p>Recognizing the importance of technology and digital leadership in student affairs, faculty members at a Western region student affairs graduate degree granting program secured funding to develop modules on digital identity, cybersecurity, multicultural technology competence, and digital leadership for graduate students and student affairs professionals. This mixed-methods exploratory investigation found that while graduate students (GSs) (<i>n</i> = 25) had higher pre-module scores compared to student affairs professionals (SAPs) (<i>n</i> = 43), the SAPs recorded higher post-module self-report scores. Graduate students’ results suggest increased confidence with all topics, especially with the Multicultural Competence module. Post-assessment means scores increased for SAPs in the Digital Leadership, Multicultural Competence, and Cybersecurity Knowledge modules, but the largest post-intervention difference was for the Digital Identity module. Across both groups, participants reported higher self-reported perceptions post-intervention. Additionally, focus groups revealed nuanced perspectives on themes of digital impression management, cybersecurity awareness, digital leadership, and multicultural competence in the digital age. A lack of instrument validation and statistical power limit broad generalization of findings. However, lessons for student affairs practitioners and digital leadership skill development are offered.</p>